Synthesis of 4-Imidazolidinones from Diamides and Ethynyl Benziodoxolones via Double Michael-Type Addition: Ethynyl Benziodoxolones as Electrophilic Ynol Synthons

Shimizu, Ayaka; Shibata, Atsushi; Kobayashi, T.; Kumai, Yuuichi; Kawakami, Ryouhei; Esaki, Hiroyoshi; Fukushima, K.; Tada, Norio; Itoh, Akichika

doi:10.1021/acs.orglett.2c03648

Cited by 8 publications

(6 citation statements)

References 41 publications

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“…459,[484][485][486][487][488][489][490][491][492][493][494][495][496] Besides, several metal-free alkynylation reactions have also been reported for the synthesis of numerous synthetically important targets, including heterocycles. [497][498][499][500][501][502][503][504][505][506][507] Representative examples for metal-catalyzed, photoredox and metal-free alkynylation reactions using EBXs are presented in Scheme 43.…”

Section: Hypervalent Heterocyclic Compounds Of Iodine(iii)mentioning

confidence: 99%

Organohypervalent heterocycles

Kumar,

Dohi,

Zhdankin

2024

Chem. Soc. Rev.

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Section: Hypervalent Heterocyclic Compounds Of Iodine(iii)mentioning

confidence: 99%

Organohypervalent heterocycles

Kumar,

Dohi,

Zhdankin

2024

Chem. Soc. Rev.

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“…Following derivatization of the 4-imidazolidinones, we con-ducted several control experiments and density functional theory calculations to gain mechanistic insight. [41] Solid-Phase Synthesis: Solid-phase synthesis techniques offer practical advantages for the synthesis of imidazolidine derivatives, particularly in the context of combinatorial chemistry. Immobilizing the growing compound on a solid support allows for efficient purification and screening of diverse compounds, expediting the optimization process.…”

Section: Other Synthesis Approaches Used For Accessing Imidazolidinon...mentioning

confidence: 99%

“…The diastereoselective synthesis of cis‐2,5‐disubstituted 4‐imidazolidinones was achieved using amino acid‐derived diamides. Following derivatization of the 4‐imidazolidinones, we conducted several control experiments and density functional theory calculations to gain mechanistic insight [41] …”

Section: Other Synthesis Approaches Used For Accessing Imidazolidinon...mentioning

confidence: 99%

Imidazolidinones Derivatives As Pioneering Anticancer Agents: Unraveling Insights Through synthesis And Structure‐Activity Exploration

Dewangan,

Rawat,

Singh Thakur

2024

ChemistrySelect

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Imidazolidinone derivatives have emerged as promising anticancer agents, captivating the attention of researchers in medicinal chemistry. Imidazolidinones, characterized by their unique chemical structure, have demonstrated versatility in synthetic methodologies. Researchers have developed a variety of derivatives, each with distinct modifications, allowing for fine‐tuning of pharmacological properties. This review explores the journey of imidazolidinone compounds, from synthesis to structure‐activity exploration, and investigates their anticancer mechanistic pathways. The synthesis methodologies, including diverse approaches and reaction conditions, were examined. Structural modifications are discussed, showing the versatility sof imidazolidinone scaffolds. Mechanistic insights into their anticancer mechanisms, in vitro, ex‐vivo and in vivo activities, with their challenges in development are critically analyzed. This paper concludes by emphasizing the potential of imidazolidinone derivatives and suggesting future research directions in the pursuit of novel and effective anticancer therapeutics.

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“…A wide range of heterocycles can be synthesized using EBXs under transition metalfree conditions [70,[145][146][147]. Cossy et al reported the synthesis of tetrahydropyrazines 134 from diamides 133 using TMS-EBX 51c in the presence of a strong base through 6-endo-dig cyclization of the ynamide intermediate A (Scheme 28a) [70].…”

Section: Transition Metal-free Reactionsmentioning

confidence: 99%

Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications

et al. 2023

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Hypervalent iodine reagents are in high current demand due to their exceptional reactivity in oxidative transformations, as well as in diverse umpolung functionalization reactions. Cyclic hypervalent iodine compounds, known under the general name of benziodoxoles, possess improved thermal stability and synthetic versatility in comparison with their acyclic analogs. Aryl-, alkenyl-, and alkynylbenziodoxoles have recently received wide synthetic applications as efficient reagents for direct arylation, alkenylation, and alkynylation under mild reaction conditions, including transition metal-free conditions as well as photoredox and transition metal catalysis. Using these reagents, a plethora of valuable, hard-to-reach, and structurally diverse complex products can be synthesized by convenient procedures. The review covers the main aspects of the chemistry of benziodoxole-based aryl-, alkynyl-, and alkenyl- transfer reagents, including preparation and synthetic applications.

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Synthesis of 4-Imidazolidinones from Diamides and Ethynyl Benziodoxolones via Double Michael-Type Addition: Ethynyl Benziodoxolones as Electrophilic Ynol Synthons

Cited by 8 publications

References 41 publications

Organohypervalent heterocycles

Organohypervalent heterocycles

Imidazolidinones Derivatives As Pioneering Anticancer Agents: Unraveling Insights Through synthesis And Structure‐Activity Exploration

Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications

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